We report the development of a multifunctional reagent for the direct conversion of carboxylic acids to aldehydes under mild conditions and with exquisite chemoselectivity. These reactions proceed in aqueous solvent at room temperature in 20 min, can be done open to air, require no metal catalysts, and employ near-stoichiometric amounts of both reducing agent and a mild base. No over-reduction, epimerization, or reduction of other reducible functional groups is observed. With this reagent, a broad scope of complex, drug-like aryl and alkyl carboxylic acids can be reduced directly to aldehydes.

2-Iodoxybenzoic acid (IBX) is a versatile oxidant used in chemical synthesis. It has been employed as a reagent in more than 1400 publications since its initial use as an oxidant described in 1994. Wh...

We report Lewis acid-catalyzed direct conversion of carboxylic acids into primary amides and nitriles using bis(trimethylsilyl)amine as an ammonia surrogate. With 1.1 equiv of bis(trimethylsilyl)amine...